Craziest Men's Style and Fashion Trends in the Last 20 Years

Generally, men care a lot less about style and fashion than women. Yet, over the past 20 years, we still managed to create some pretty terrible styles that were followed by our fellow men and encouraged to the point of becoming acceptable trends. Here are some of the most ridiculous mens style and fashion trends we have seen since the early 1990s.

Trucker Hats

Ashton Kutcher will be seen a couple times on this list, but it was his popularizing of the trucker hat in the early 2000s that was his most egregious fashion fault.

Generally, men care a lot less about style and fashion than women. Yet, over the past 20 years, we still managed to create some pretty terrible styles that were followed by our fellow men and encouraged to the point of becoming acceptable trends. Here are some of the most ridiculous mens style and fashion trends we have seen since the early 1990s.

Trucker Hats

Ashton Kutcher will be seen a couple times on this list, but it was his popularizing of the trucker hat in the early 2000s that was his most egregious fashion fault.

glamourmagazine.co.uk

Cell Phone Belt Clips

Typically can be seen on the belt of the same guy rocking a bluetooth earpiece.

Cell Phone Belt Clips

Typically can be seen on the belt of the same guy rocking a bluetooth earpiece.

geeksugar.com

Guyliner

Synonymous with emo, metrosexuality and Peter Parker in "Spider-Man 3," eyeliner for guys is a style trend that should never come back.

Guyliner

Synonymous with emo, metrosexuality and Peter Parker in "Spider-Man 3," eyeliner for guys is a style trend that should never come back.

Steve Granitz/WireImage.com

Frosted Tips

Men bleaching all of their hair was also an inexplicable style craze once, but frosted tips may have been worse.

Frosted Tips

Men bleaching all of their hair was also an inexplicable style craze once, but frosted tips may have been worse.

Let's be honest. Most men who wore wallet chains didn't have the bankroll to warrant the wallet security anyway.

Wallet Chains

Let's be honest. Most men who wore wallet chains didn't have the bankroll to warrant the wallet security anyway.

Thinkstock

Shell Necklaces

We'll ignore the country hat since Kenny Chesney is a country music star, but there's really no excuse for him rocking the tight puka shell necklace.

Shell Necklaces

We'll ignore the country hat since Kenny Chesney is a country music star, but there's really no excuse for him rocking the tight puka shell necklace.

countryuniverse.net

Mullets

The mullet-mania of the 1990s resulted in a lot of laughs and maybe peaked with the 2001 movie "Joe Dirt," but no self-respecting man should ever consider sporting one (unless they lost a bet and have to pay up).

Mullets

The mullet-mania of the 1990s resulted in a lot of laughs and maybe peaked with the 2001 movie "Joe Dirt," but no self-respecting man should ever consider sporting one (unless they lost a bet and have to pay up).

mulletjunky.com

Jean Shorts

Also known as jorts, no fashion trend will make you look more like a dorky dad than jean shorts...except for maybe the fanny pack.

Jean Shorts

Also known as jorts, no fashion trend will make you look more like a dorky dad than jean shorts...except for maybe the fanny pack.

Fanny Packs

If you would like to be able to carry all of your valuables in one convenient bag, get a girlfriend and take advantage of her purse.

Fanny Packs

If you would like to be able to carry all of your valuables in one convenient bag, get a girlfriend and take advantage of her purse.

Ear Gauges

Have you ever looked at your earlobe and thought, "Man, I really wish I could stick my finger through there?" For alternative rockers everywhere, the answer was yes.

Ear Gauges

Have you ever looked at your earlobe and thought, "Man, I really wish I could stick my finger through there?" For alternative rockers everywhere, the answer was yes.

Chey Rawhoof/Flickr

Manpris

Not quite shorts, not quite pants, not quite cool.

Manpris

Not quite shorts, not quite pants, not quite cool.

thedetailedimage.com

Bling Bling

Worn by hip hop artists, drug dealers and athletes who just signed multimillion dollar contracts. The more bling you wear, the higher your perceived social status, and the more likely you are to one day file for bankruptcy.

Bling Bling

Worn by hip hop artists, drug dealers and athletes who just signed multimillion dollar contracts. The more bling you wear, the higher your perceived social status, and the more likely you are to one day file for bankruptcy.

ebaumsworld.com

Seinfeld Style

Colorful button-up shirts sometimes tucked into mom jeans and complemented with sneakers was a look that never hindered Jerry's ability to pick up women, but it's one that should never be imitated again.

Colorful button-up shirts sometimes tucked into mom jeans and complemented with sneakers was a look that never hindered Jerry's ability to pick up women, but it's one that should never be imitated again.

This outrageous brand of pants was popular in the early 1990s and can still be found in the drawers of overweight football fans to this day.

Zubaz

This outrageous brand of pants was popular in the early 1990s and can still be found in the drawers of overweight football fans to this day.

laist.com

Sweat Suits

Worn by basketball coach Bob Huggins and wannabe mafia types. Full-body comfort will not disguise the fact that a slob is underneath.

Sweat Suits

Worn by basketball coach Bob Huggins and wannabe mafia types. Full-body comfort will not disguise the fact that a slob is underneath.

Andy Lyons/Getty Images

Socks With Sandals

Before he became Snoop Lion, he was just Snoop Lazy.

Socks With Sandals

Before he became Snoop Lion, he was just Snoop Lazy.

Jeffrey Ufberg/WireImage.com

Carpenter Jeans

Should only be worn by real carpenters. No exceptions.

Carpenter Jeans

Should only be worn by real carpenters. No exceptions.

dickies.com

Chinstrap Beards

It takes way too much time and effort to groom your beard into a nice thin line around your face, especially when said thin line beard makes you look like an A-hole.

Chinstrap Beards

It takes way too much time and effort to groom your beard into a nice thin line around your face, especially when said thin line beard makes you look like an A-hole.

menshair.about.com

Deep V-Necks

If you are constantly complaining about having an abnormally warm chest and need to get it some air, a deep V is OK. Otherwise, do not wear them.

Deep V-Necks

If you are constantly complaining about having an abnormally warm chest and need to get it some air, a deep V is OK. Otherwise, do not wear them.

mensfashion.about.com

Ed Hardy/Affliction Attire

Any style related to the men of "Jersey Shore" should be avoided like the plague.

Ed Hardy/Affliction Attire

Any style related to the men of "Jersey Shore" should be avoided like the plague.

zimbio.com

Flat Bill Hats with the Sticker On

This is one of those fashion trends that had to have started by accident. Perhaps it went down like this:

Guy 1: Hey man, cool new hat, but you forgot to take the sticker off.

Guy 2 (embarrassed): Uhh, no! I meant to leave it on. It's a cool new style that everyone's doing.

Guy 1 (stupid): Sweet!

Flat Bill Hats with the Sticker On

This is one of those fashion trends that had to have started by accident. Perhaps it went down like this:

Guy 1: Hey man, cool new hat, but you forgot to take the sticker off.

Guy 2 (embarrassed): Uhh, no! I meant to leave it on. It's a cool new style that everyone's doing.

Guy 1 (stupid): Sweet!

The Soul Patch

"America's Got Talent" judge and apparent comedian Howie Mandel is practically hairless, except for the creepy triangle of facial hair he keeps below his bottom lip. It's commonly viewed as a sad attempt to be youthful and edgy...which also explains the double hoop earrings.

The Soul Patch

"America's Got Talent" judge and apparent comedian Howie Mandel is practically hairless, except for the creepy triangle of facial hair he keeps below his bottom lip. It's commonly viewed as a sad attempt to be youthful and edgy...which also explains the double hoop earrings.

George Pimentel/Getty Images

Layered Polos

Along with popping collars, this fashion trend blew up sometime around 2002-2003, and frat houses have never been the same (just kidding, they are still exactly the same).

Layered Polos

Along with popping collars, this fashion trend blew up sometime around 2002-2003, and frat houses have never been the same (just kidding, they are still exactly the same).

complex.com

Bowl (Mushroom) Haircut

In the early 90s, not only did many young men and boys have mushroom haircuts, they were proud of it. You weren't cool unless your mom put a bowl around your head and trimmed the hair underneath. Makes sense.

Bowl (Mushroom) Haircut

In the early 90s, not only did many young men and boys have mushroom haircuts, they were proud of it. You weren't cool unless your mom put a bowl around your head and trimmed the hair underneath. Makes sense.

JNCO Jeans

These insanely wide boys and mens jeans gained recognition in the 90s, and gobbled up the shoes of many skaters, ravers and Juggalos in the process. They looked like someone took two large jean skirts, sewed them together, added some large pockets and sewed crazy emblems on at the end.

JNCO Jeans

These insanely wide boys and mens jeans gained recognition in the 90s, and gobbled up the shoes of many skaters, ravers and Juggalos in the process. They looked like someone took two large jean skirts, sewed them together, added some large pockets and sewed crazy emblems on at the end.

styleforum.com

Nameplate Belts

It doesn't matter what word you were displaying on your belt, the message was the same: JACKASS.

Nameplate Belts

It doesn't matter what word you were displaying on your belt, the message was the same: JACKASS.

myflyculture.com

Parachute Pants

MC Hammer's super hit single "U Can't Touch This" came out in 1990, yet the silly pants he wore and made popular were widely accepted as an OK style for many years to come. What were we all thinking?

Parachute Pants

MC Hammer's super hit single "U Can't Touch This" came out in 1990, yet the silly pants he wore and made popular were widely accepted as an OK style for many years to come. What were we all thinking?

Sagging

When your underpants are no longer under your pants, you just look like a damn fool.

Sagging

When your underpants are no longer under your pants, you just look like a damn fool.

fashionindie.com

Tall Tees

XXL t-shirts for guys who belong in the medium section. There is no explanation for wanting to wear a shirt that is more like a dress, but if your saggy jeans fall off it may come in handy.

Tall Tees

XXL t-shirts for guys who belong in the medium section. There is no explanation for wanting to wear a shirt that is more like a dress, but if your saggy jeans fall off it may come in handy.

allhiphop.com

Pointy Shoes

Widely regarded by hot women like Hope Dworaczyk as the most hated mens fashion trend, pointy toe shoes will make you look as desirable as the Keebler Elf.

Pointy Shoes

Widely regarded by hot women like Hope Dworaczyk as the most hated mens fashion trend, pointy toe shoes will make you look as desirable as the Keebler Elf.

fashionbombdaily.com

Skinny Jeans

"They're kinda 'in' right now" is something that losers say. If you own them, they should remain 'in' your closet.

Skinny Jeans

"They're kinda 'in' right now" is something that losers say. If you own them, they should remain 'in' your closet.

YouTube/kirkzipfel

Tight-Rolled Jeans

A carryover from the ridiculous style of the 1980s, tight-rolling your jeans was a good way to fit in with the cool crowd in the early 90s - and also keep your socks from falling down.

Tight-Rolled Jeans

A carryover from the ridiculous style of the 1980s, tight-rolling your jeans was a good way to fit in with the cool crowd in the early 90s - and also keep your socks from falling down.

Visors

How an article of clothing that should only be worn on the golf course made its way to the mainstream and got turned backwards and flipped upside down is beyond me, but Jamie Kennedy sure is grateful.

Visors

How an article of clothing that should only be worn on the golf course made its way to the mainstream and got turned backwards and flipped upside down is beyond me, but Jamie Kennedy sure is grateful.

my350z.com

Wind Pants

The ironic part about wind pants is that they are most useless when you are out in a lot of wind. Yet, walking around in garbage bag material pants was once widely accepted and deemed appropriate. Consumers are idiots.

Wind Pants

The ironic part about wind pants is that they are most useless when you are out in a lot of wind. Yet, walking around in garbage bag material pants was once widely accepted and deemed appropriate. Consumers are idiots.

Grills

Also spelled Grillz (if you're cool). Most people try to avoid dental work, but in the hip hop culture in the mid-2000s, Dirty South rap started to rise and mouth jewelry became highly sought after. They may cost a lot and lead to further dental health problems, but if Paul Wall and Lil Jon are doing it we all better jump on board!

Grills

Also spelled Grillz (if you're cool). Most people try to avoid dental work, but in the hip hop culture in the mid-2000s, Dirty South rap started to rise and mouth jewelry became highly sought after. They may cost a lot and lead to further dental health problems, but if Paul Wall and Lil Jon are doing it we all better jump on board!